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Optimization of synthetic parameters of high-purity trifunctional mercaptoesters and their curing behavior for the thiol–epoxy click reaction

The direct esterification reaction between 3-mercaptopropionic acid (3-MPA) and trimethylolpropane (TMP) was conducted in the presence of various catalyst concentrations of p-toluenesulfonic acid (p-TSA) to examine the optimized synthetic conditions needed to produce high-purity trimethylolpropane-t...

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Autores principales: Hong, Seung-Mo, Kim, Oh Young, Hwang, Seok-Ho
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9042355/
https://www.ncbi.nlm.nih.gov/pubmed/35497273
http://dx.doi.org/10.1039/d1ra05981e
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author Hong, Seung-Mo
Kim, Oh Young
Hwang, Seok-Ho
author_facet Hong, Seung-Mo
Kim, Oh Young
Hwang, Seok-Ho
author_sort Hong, Seung-Mo
collection PubMed
description The direct esterification reaction between 3-mercaptopropionic acid (3-MPA) and trimethylolpropane (TMP) was conducted in the presence of various catalyst concentrations of p-toluenesulfonic acid (p-TSA) to examine the optimized synthetic conditions needed to produce high-purity trimethylolpropane-tris(3-mercaptopropionate) (TMPMP). The purity of the desired TMPMP and uncompleted side-product reduced as the acid catalyst concentration in this esterification reaction increased while the generation of thioester-based side-product increased. The equivalent ratio between epoxy and the manufactured TMPMP was maintained at 1 : 1 to monitor the curing behavior of the thiol–epoxy click reaction using the DSC technique. The thermal features of the base-catalyzed TMPMP-cured epoxy resin were assessed according to the purity of the TMPMP curing agent.
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spelling pubmed-90423552022-04-28 Optimization of synthetic parameters of high-purity trifunctional mercaptoesters and their curing behavior for the thiol–epoxy click reaction Hong, Seung-Mo Kim, Oh Young Hwang, Seok-Ho RSC Adv Chemistry The direct esterification reaction between 3-mercaptopropionic acid (3-MPA) and trimethylolpropane (TMP) was conducted in the presence of various catalyst concentrations of p-toluenesulfonic acid (p-TSA) to examine the optimized synthetic conditions needed to produce high-purity trimethylolpropane-tris(3-mercaptopropionate) (TMPMP). The purity of the desired TMPMP and uncompleted side-product reduced as the acid catalyst concentration in this esterification reaction increased while the generation of thioester-based side-product increased. The equivalent ratio between epoxy and the manufactured TMPMP was maintained at 1 : 1 to monitor the curing behavior of the thiol–epoxy click reaction using the DSC technique. The thermal features of the base-catalyzed TMPMP-cured epoxy resin were assessed according to the purity of the TMPMP curing agent. The Royal Society of Chemistry 2021-10-22 /pmc/articles/PMC9042355/ /pubmed/35497273 http://dx.doi.org/10.1039/d1ra05981e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Hong, Seung-Mo
Kim, Oh Young
Hwang, Seok-Ho
Optimization of synthetic parameters of high-purity trifunctional mercaptoesters and their curing behavior for the thiol–epoxy click reaction
title Optimization of synthetic parameters of high-purity trifunctional mercaptoesters and their curing behavior for the thiol–epoxy click reaction
title_full Optimization of synthetic parameters of high-purity trifunctional mercaptoesters and their curing behavior for the thiol–epoxy click reaction
title_fullStr Optimization of synthetic parameters of high-purity trifunctional mercaptoesters and their curing behavior for the thiol–epoxy click reaction
title_full_unstemmed Optimization of synthetic parameters of high-purity trifunctional mercaptoesters and their curing behavior for the thiol–epoxy click reaction
title_short Optimization of synthetic parameters of high-purity trifunctional mercaptoesters and their curing behavior for the thiol–epoxy click reaction
title_sort optimization of synthetic parameters of high-purity trifunctional mercaptoesters and their curing behavior for the thiol–epoxy click reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9042355/
https://www.ncbi.nlm.nih.gov/pubmed/35497273
http://dx.doi.org/10.1039/d1ra05981e
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